Hydroxy-1,4-benzoquinone

Hydroxy-1,4-benzoquinone

Names
IUPAC name 2-hydroxycyclohexa-2,5-diene-1,4-dione
Other names 2-Hydroxy-p-benzoquinone
Identifiers
CAS Number	2474-72-8
3D model (Jmol)	Interactive image
ChEBI	CHEBI:18400
ChemSpider	133103
PubChem	151011
UNII	C7I5HV2JFI
InChI InChI=1S/C6H4O3/c7-4-1-2-5(8)6(9)3-4/h1-3,9H Key: GPLIMIJPIZGPIF-UHFFFAOYSA-N InChI=1/C6H4O3/c7-4-1-2-5(8)6(9)3-4/h1-3,9H Key: GPLIMIJPIZGPIF-UHFFFAOYAA
SMILES C1=CC(=O)C(=CC1=O)O
Properties
Chemical formula	C6H4O3
Molar mass	124.1 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Hydroxy-1,4-benzoquinone, also called hydroxy-para-benzoquinone, is an organic compound with formula C
6H
4O
3, formally derived from 1,4-Benzoquinone by replacing one hydrogen atom with a hydroxyl (OH) group. It is one of three hydroxybenzoquinone isomers and one of the simplest hydroxyquinones.

The compound is often called 2-hydroxy-1,4-benzoquinone, but the "2-" prefix is superfluous since there is no other hydroxy derivative of 1,4-benzoquinone. The IUPAC name is 2-hydroxycyclohexa-2,5-diene-1,4-dione.

It is formed by the reaction of 1,4-benzoquinone with hydrogen peroxide and is a byproduct of the metabolism of phenols, such as 1,2,4-benzenetriol.^[1] The enzyme 1,2,4-benzenetriol dehydrogenase catalyzes the conversion of 1,2,4-benzenetriol to 2-hydroxy-1,4-benzoquinone, and the enzyme hydroxybenzoquinone reductase catalyzes the reverse reaction. The enzyme 2-hydroxy-1,4-benzoquinone-2-reductase converts it to 1,4-benzoquinone.

It tends to dimerize spontaneously by peroxo bridges.^[1]

See also

• Tetrahydroxy-1,4-benzoquinone

References

1. Philipp, B; Schink, B (1998). "Evidence of two oxidative reaction steps initiating anaerobic degradation of resorcinol (1,3-dihydroxybenzene) by the denitrifying bacterium Azoarcus anaerobius". Journal of Bacteriology. 180 (14): 3644–9. PMC 107334. PMID 9658009.